


so many ways (to enjoy life)

by LilMysterios



Series: he who used to be free [2]
Category: Supernatural
Genre: Alternate Universe - Pirate, Anal Fingering, Anal Plug, Blow Jobs, Bottom Castiel, Captain Dean Winchester, Creampie, Crying, Dean is an attentive captain, Dirty Talk, Double Penetration, F/M, Gangbang, Glory Hole, Hand Jobs, Humiliation, M/M, Merpeople are real, Non-Consensual Bondage, Orgasm Denial, Plot What Plot/Porn Without Plot, Prostate Massage, Prostitution, Public Sex, Sexual Slavery, Speeches, Virginity, but he is human now, merman cas
Language: English
Status: Completed
Published: 2015-05-03
Updated: 2015-05-03
Packaged: 2018-03-28 19:56:20
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 1
Words: 2,031
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3867853
Author URL: https://archiveofourown.org/users/LilMysterios/pseuds/LilMysterios
Summary: <blockquote class="userstuff">
              <p>What happens exactly when you put a tiny, scared merboy in the middle of horny pirates, and leave him there.</p>
            </blockquote>





	so many ways (to enjoy life)

**Author's Note:**

> As usual, everything is in the tags and warnings, so if what is described literally right above this isn't your cup of tea, please do yourself a favor and don't read this fic.  
> And if it is your cup of tea, welcome aboard! (but still, don't hesitate to tell me if you feel tags should be added)
> 
> This work was beta'd by harleyquinnnapier, but if you spot any mistake I'll be happy to correct them! ^^

 

The men of the crew couldn’t wait for the captain’s return, and Adam was definitely the most impatient of all.

 _I have a surprise for all of you_ , the captain had said a few minutes earlier, his tone mysterious and promising, before ducking back into his quarters.

Adam knew the captain’s surprises were always incredible, and he had to fight the instinct to bounce around in his eagerness to discover what the great Dean Winchester had planned for them this time.

Adam himself, as the newest crewmember and humble ship’s boy, had never been lucky enough to partake in one of those infamous celebrations, but the others had told him enough to have him tremble in anticipation.

Like the time Dean had bought them a night with a cheap harbor’s whore, leaving them to enjoy her many talents from dusk to dawn… Benny still laughed when he remembered how she had left limping, thick come gushing out of both her holes, dripping between her thighs and down to her ankles.

“ _She screamed all night long_ ,” he had said proudly to an impressed Adam, “ _while we took care of all her hungry holes… pirates are really something else, I guess she hadn’t been notified._ ”

Or the time after they had boarded on a cruise ship, and Dean had let them do what they wanted with the passengers… the night had echoed with screams and cries while they had taken their pleasure with the wives and daughters of the rich travellers… Adam could still hear the vivid story that Sam had told him about the girl he had chosen that night.

“ _She was blond, lovely… a virgin, of course,_ ” had described Sam, wistful melancholy in his hazel eyes. “ _Had never been touched by a man… God, she was so warm, so tight…_ ”

He had smiled, a ruthless show of pointy teeth.

“ _Of course after a few days with me and the other guys, all her holes were as used as an old whore’s._ ”

Adam had laughed, picturing the girl (Sam liked them real young) moaning and squirming on Sam’s enormous cock, her wet, tight pussy stretched wide around him while some other man joined in from behind, forcing her asshole open with his dick.

“ _She died not long after… life on seas wasn’t really for her, I guess_.”

Or the time when the captain had ordered the raid of a village (something about the chief refusing to pay his debts, Adam wasn’t really sure), and the pirates had invaded the houses, killing every man and raping every woman old enough to take a dick… rumor said that, in the following year, no less than twenty-eight births had repopulated the ruined village.

Adam loved those glorious stories of freedom and savagery, and he longed for the day he could truly become part of the crew…

But when the captain exited his quarters, holding a rope behind him, Adam knew immediately that this time would be different.

That this surprise would be the best of all.

“Gentlemen,” called Dean.

They all gathered around him, curious about the reason around all this secrecy, and Adam could feel his heart beating faster.

“You are exceptional men,” started the captain.

The pirates showed their agreement with a loud clamor.

“You are loyal to me, you are ferocious and you would go to every mean for your captain… and you know I see you all as my brothers.”

A new enthusiastic shout.

“But you are still my crew, my responsibility, and I want all of your needs to be fulfilled as long as you serve under my command,” declared Dean. He paused for a handful of seconds, making sure he had the attention of every man present on the deck. “I believe I have finally found the perfect way to satisfy all of you, and the one thing that won’t put at risk this group’s cohesion.”

He pulled gently on the rope, and a small frame appeared behind him, still hidden in the shadows…

Adam held his breath.

“This is Castiel,” announced Dean and a second later their long-awaited surprise stepped into the light.

When all men could finally see the captain’s mysterious gift, there was a stunned silence, and even Adam blinked, wanting to make sure he wasn’t dreaming.

It was a boy.

A small, naked boy, breathtakingly lovely, his pale legs thin and smooth and his rosy nipples cheekily hardened in the sea breeze, soft little penis nestled between slender thighs… Adam heard several men let out groans of desire, and himself felt his cock twitch in his pants.

“Castiel is a merboy,” said Dean.

Adam felt the rush of electric tension that ran through the crew like a live wire, and he himself suppressed a shiver. Merpeople were supposed to be hidden and legendary, impossible to catch a glimpse of and even more impossible to catch… he would never have guessed that the exquisite creature standing naked and glowing in front of them was part of the people who lived in the depths of the sea.

“At least he was one,” continued Dean with a smile that showed an intense satisfaction, “until I found him in one of our lifeboats, disorientated and made human by dehydration… and took his virginity.”

The crewmen had a similar reaction of stunned awe, for the legend said that taking a merperson’s virginity while they were still in human form would condemn them to stay in this shape forever.

“From now on, Cas here is human, and will stay that way,” confirmed Dean calmly, “and I really want him to live with us, on this ship.”

Adam could feel the important part of the surprise coming.

“I know that some of you suffer from the abstinence forced on you by our constant travelling,” explained Dean, “and I think that Cas should be able to free you from quite a bit of that tension.”

Next to Adam, a few pirates laughed softly, getting where the captain was going with this.

“Obviously, he is and will remain my property,” added Dean with a smile. “But it’ll be my pleasure to leave him at your disposition during the day, only to retrieve him at nightfall.”

He stroked a possessive hand against the merboy’s backside, and the creature startled, its huge blue eyes blinking fearfully; Adam could feel his cock harden in his pants.

“Questions?” Dean asked, patient gaze running through his crew. “No? Good… then I’ll leave you to your introductions.”

He swiftly untied the rope tying his merboy’s hands together and stepped away, retrieving to his quarters.

Castiel, since that was his name, was left in the middle of the deck, naked and trembling, and Adam distinctly saw Sam lick his lips as they formed a circle around him.

Yeah, thought Adam as a whimpering Castiel was forced on his knees, pale ass cheeks spread by rough hands to reveal a perfect, pink little fuckhole…

This was definitely the best surprise _ever_.

*

The arrival of their new toy brought a rush of passion amongst the crewmen.

It wasn’t uncommon to walk through the deck and see Cas being taken by two enthusiastic pirates, one spreading the round ass cheeks with massive, hairy hands, to watch his thick cock plunge in and out of Cas’ stretched hole, and the other brutally fucking Cas’ throat, eyes closed in bliss and oblivious to the creature’s plaintive whimpers as his erection slid between red, abused lips…

More than once, Adam came back from the hold to see Cas being the center of a circle of men, every single part of his body dedicated solely to their pleasure…

His small hands, one on each side, would be caressing large, already-dripping erections.

His lips would be stretched obscenely around a huge cock, his throat outlining the pirate’s thrusts as the man ruthlessly face-fucked him.

Another man would be rubbing his erection through Castiel’s come-stained hair, one hand on his dick and the other pinching cruelly a pink nipple, making Castiel whimper at the torturous tweak of his thick fingers.

Two last men would be busy enjoying the boy’s sweet, tight little ass, one lying on the wood of the deck with Cas bouncing on his huge cock, and the other with his dick alongside the first’s, deep inside Cas and attempting to follow the rhythm.

The other men, those who already had had their turn and those who would soon, would be standing nearby, stroking themselves slowly, their eyes glued to their toy’s lithe, pale body and the way he arched his back in both pain and forced pleasure, weak and helpless and broken.

All his moans and whimpers would drown in the sound of their exclamations of excitement and pleasure.

“That’s it, little boy, take my cock, take it deep… c’mon, swallow it all,” one would be saying, and Cas would choke on his dick.

“This is what you were made for, right, little fish?” would exclaim another. “Never seen such a tight ass, made to be fucked, to be pounded and ripped apart, again and again and _again_ …”

“You love spreading your thighs for us, don’t you?” would laugh a third one. “You’re always such a tease, such a little cockslut, making us want with your little hole on display… you only get what you deserve, you _slut_.”

Cas never said anything, his eyes wide and scared, and he panted while all those cocks used him one by one.

*

If no one was enjoying Cas, then he was tied to the mast, thighs spread and body folded uncomfortably, positioned so that his ass was presented at any moment… the crewmen had been ordered to never leave Cas empty after they had taken their pleasure, and so his hole was at all times filled with a large ivory plug, a purchase the captain had been told was perfect to _keep a tight hole always stretched and ready, always available_.

A passer-by, like often Adam, could easily take the plug out of Cas and play for a few minutes with his wet, gaping warm hole… it one was of Adam’s favorite things to do with Cas, because he could see every on of the merboy’s reactions, watch the tears roll on his pretty face as Cas humped the air, nipples raised and hard little prick desperate for a bit of friction… but then Adam always pulled his fingers out, licked Cas’ tears off his face and put the plug back into place, thrusting it experimentally a couple times against Cas’ prostate before settling the device as deep as it would go and leaving the boy there, wanton and frustrated.

*

The captain, an inventor at heart and never short of ideas to better put his little whore to use, even imagined a clever device, that he had made in a foreign port by some carpenter…

It was a wooden box, just big enough to allow Cas to fit in it on all fours, and pierced strategically on both sides, one overture against the boy’s ass and one in front of his mouth.

The captain liked to take the box out on the decks, settling it in plain view, and rent his toy to the passers-by… of course the display attracted quite a lot of curiosity, and soon queues were organized, every man waiting patiently in line for his turn to pay ten dollars, slide his cock into a warm, well-used hole, and enjoy eight to ten minutes of pure bliss inside a hot, slick passage.

At the end of the day, Dean brought the box back on the ship and his men helped take Cas out, body covered in come, jaw aching and hole raw and abused-red after being fucked by so many men… Adam always volunteered to smear Cas’ hole with soothing salve, delighted like he was every time he could stuff his fingers inside Cas for a totally innocent reason.

*

Really, the ways to use Cas and his perfect little holes were endless, and everyone on the ship loved trying to come up with new ones…

In fact, they had trouble remembering a time before Cas’ arrival, for they had never been so profoundly satisfied in every way.

 

**Author's Note:**

> Sooooo... I have some ideas and a bit of beginning written for a third part, but it would probably be a little different... so tell me if you'd like to read more of this.
> 
> Anyway I hope you liked it, and if you did, don't forget ; kudos are love!  
> (and, well, comments are like a wonderful, celestial kind of love, but I know that might be too much pressure XP)
> 
> Have a great day!


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